I have a copyright question for you, in regards to the publication of artwork.
A very talented friend of mine has a business painting portraits of childhood toys. Parents (or generally nostalgic adults) send her their photos of favourite toys, dolls, plush animals, etc., and commission a beautiful expressionistic portrait on canvas. This business is growing, due to the quality of the artwork. She is now interested in putting together a book featuring this artwork, to submit to an agent. However, she's concerned there might be copyright infringent issues at hand, because so many of the subjects in these paintings are recognisable as commercially produced toys.
For instance, she knows that a stuffed 'Hello Kitty' toy is already protected by a world of trademarks and copyright laws. Would a painting of it create a minefield for a potential publisher?
Yes. I think it probably would. And there's something else you haven't mentioned: people have paid for these artworks. That means they own them. That means that the artist can't just put them in a book unless she has express permission from the owners of the artwork, especially as she's creating these works on commission - the owners of the toys (or their parents) have asked her to do the paintings, so they're not her original idea. Even if the toy isn't as recognisable as Barbie, the owners of the toy may not like having it depicted in a book.
Presuming that all of the toy/artwork owners have given permission, there could be issues of trademark (more trademark than copyright). I don't know intellectual property law as well as I used to, so I can't say what's allowable in terms of artwork. Some things are allowable if they're 'satire' but I don't know whether or not there are other exemptions - it's possible that if she'd painted Hello Kitty wearing a hula skirt it would be easier to put the painting in a book than a straight-up portrait. A straight-up portrait could be considered 'passing off'.
The best thing for your friend to do is to seek a legal opinion before she does anything else. She needs an opinion on her ability to reproduce the works and also on the content of the works. An intellectual property lawyer specialising in copyright and trademark should be able to help, and $300 or however much they charge per 6 minutes (joking! I'm sure you get at least 12 minutes for that much money) is, actually, not a lot to pay to either know she's in the clear or to avoid doing a large amount of work - putting the book together, submitting to publishers - for nothing. Why spend a lot of time worrying about it when you can pay a professional to put your mind at ease? Now, if I can just get an IP lawyer to sponsor this blog ...